Palladium-Catalyzed Allylation of Vinylethylene Carbonates with β-Ketophosphonates: Stereoselective Synthesis of (Z)-Homoallylic Phosphonates

A first simple palladium catalyzed allylation of vinylethylene carbonates with beta-ketophosphonates has been developed. This method provides access to (Z)-tri- and tetrasubstituted homoallylic phosphonates with exclusive regioselectivity, chemoselectivity and (Z)-stereoselectivity. The reaction tolerates a wide substrate scope of vinylethylene carbonates and beta-ketophosphonates with electron-donating and electron-withdrawing groups and works well on the gram scale.

Automated summary

A first simple palladium catalyzed allylation of vinylethylene carbonates with beta-ketophosphonates has been developed, providing access to (Z)-tri- and tetrasubstituted homoallylic phosphonates with exclusive regioselectivity, chemoselectivity and (Z)-stereoselectivity. The reaction tolerates a wide substrate scope and works well on the gram scale.